Saturated ethylamine derivatives



Patented Feb. 4, 1941 UNITED STATES 2,230,752 SATURATED ETHYLAMINE DERIVATIVES Wilfrid Klavehn,

Heidelberg, Germany, assignors to E.

Corporation No Drawing.

3 Claims.

This invention relates to new and valuable chemical compounds which are saturated derivatives of ethylamine of the general formula R -N-R wherein R1 is an alkyl radical having six carbon atoms in a straight or branched chain, R2 is hydrogen or a lower alkyl radical, and R3 is an alkyl radical having one, three or five carbon atoms, or cycloalkyl.

These compounds modic properties.

R1 is a straight chain or branched chain, hexyl radical. R2 may be hydrogen, an alkyl radical, for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, isoamyl, etc. R3 is likewise an alkyl radical containing one, three or five carbon atoms, for example of the kind mentioned with respect to R2 or cycloalkyl, for example, cyclopentyl, cyclohexyl, methyl cyclohexyl radicals and the like.

The production of the new compounds is effected by treating saturated alkylethylamines of the formula:

have favourable antispas- As alkylating agents there may be employed,

a for example di-methyl sulphate or di-ethyl sulphate. Another group of alkylating agents are the alkyl halides such as butyl, isobutyl or isoamyl halides, for example, the iodides or bromides. Finally, the alkylation of the initial amines may be effected by condensation with aldehydes or ketones and simultaneous reduction.

For the production of cycloalkyl derivatives of the initial amines known cycloalkylating agents may be employed. The initial amines may for example be condensed with cycloaldehydes or cycloketones and simultaneously reduced.

Schwetzingen, and Anton Wolf,

Bilhuber Application February 12, 1938, Serial No. 190,326. In

Germany February 15,

Finally, as aralkylating agents there may be employed benzyl chloride, benzaldehyde and hydrogen, phenylethyl chloride, phenylacetaldehyde and hydrogen etc.

Examples 1. 26 gms. of amino-'Z-octane,

CH3.(CH2) 5.CH.(NH2) .CH3

were condensed with 17 gms. of cyclopentanone on the Water bath and then dissolved in 200 cos. of alcohol and subjected to reduction on the water bath with 20 gms. of activated aluminium. The working up was effected by the usual processes.

The cyclopentylamino-2-octane, C13I-I21N obtained boils at C. under 9 mm. pressure as a colourless oil of slight basic odour. The hydrochloride crystallised from alcohol-ether in needles of melting point 105 C.

2. 42 gms. of methylamino-Z-octane,

CH3(CH2) 5.0K. (NI-LCI-Is) .CHs

were heated with 15.5 gins. of isoamyl bromide under a reflux condenser and the reaction mixture was taken up in dilute mineral acid and the aqueous solution shaken out with ether for the removal of the non-basic portion. The base separated on the addition of alkali. The tertiary base, methylisoamyl amino 2 octane, C14H31N obtained boils at C. under 15 mm. pressure. The yield was 60% of the theoretical.

What We claim is:

1. Saturated derivatives of ethyl amine of the general formula wherein R1 is an alkyl radical containing six carbon atoms, R2 is a radical selected from the group consisting of hydrogen and lower alkyl radicals, R3 is a radical selected from the group consisting of alkyl, containing one, three and iive carbon atoms, and cycle alkyl radicals.

2. Cyclopentylamino-2-octane. 3. Methylisoamyl-amino-Z-octane.

WILFRID KLAVEl-IN. ANTON WOLF. 

